Sept. 18, 2022

Building a meaningful career | Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)

Jason Shah has led product teams at Amazon, Airbnb, Microsoft, and Yammer and currently leads the product team at Alchemy (one of the most important web3 infrastructure companies). In addition, he’s an advisor, investor, and two-time founder. In today’s episode, Jason discusses what it’s like to be a PM in web3, why his role at Amazon made such a big impact on his life and career, what makes a great leader, and how to hire well. He also shares his unique perspective on building a meaningful career and life.

Where to find Jason Shah:

• Twitter:

• LinkedIn:

• Website:

Where to find Lenny:

• Newsletter:

• Twitter:

• LinkedIn:

Thank you to our wonderful sponsors for making this episode possible:

• Whimsical:

• Coda:

• Amplitude:


Creative Selection: Inside Apple’s Design Process During the Golden Age of Steve Jobs:

• Casey Winters on Lenny’s Podcast:

• Jason Shah in Lenny’s newsletter:

The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers:

• Polygon:

• Solana:

• MoonPay:

The Vietnam War series by Ken Burns:

• Alchemy:

In this episode, we cover:

(04:31) Jason’s background

(08:19) The current state of web3

(12:44) The evolution of product management in web3

(15:27) The value of a great product manager

(18:11) Why Amazon was a great learning experience 

(20:25) A look into Amazon’s process on working backward

(23:55) How to communicate clearly

(28:17) Working backward from excitement

(32:46) What makes a great leader

(38:26) How to influence a CEO or founder’s direction 

(46:19) The career ladder vs. career map framework

(52:27) When to follow a new opportunity vs. when to stick it out

(58:50) How to hire the right people

(1:03:47) What skill is most important for product managers

(1:06:49) Lightning round!

Production and marketing by For inquires about sponsoring the podcast, email

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Jason Shah (00:00:00):

Pushback is, I couldn't imagine a word more viscerally that makes you feel like you're sort of physically going against what somebody else wants, and it gears people into a mindset of then, well, how should I push back. It starts from a place of I need to disagree, I need to say no. It's a very negative mindset, purely based on the word that has come to label a behavior that alternatively could be about how do I shift the direction on something, or how do I help the business actually succeed when I disagree with somebody about something, and that's a very different mindset. And so, the two things that I've seen be most successful would be, I think number one is actually understanding what a goal is or what somebody's kind of issue is with something, and then actually aligning those things in some way.

Lenny (00:00:53):

Welcome to Lenny's Podcast. I'm Lenny, and my goal here is to help you get better at the craft of building and growing products. I interview world-class product leaders and growth experts to learn from their hard-won experiences building and scaling today's most successful companies. Today my guest is Jason Shah. I was lucky to work with Jason while I was at Airbnb, and when I started working on this podcast, I knew that I wanted to have Jason on. He was actually my very first guest on this podcast when I was pre-recording some episodes, but as you'll hear in our chat, we decided to take another crack at it for reasons you'll soon understand.

Lenny (00:01:28):

In this episode, we cover what it's like to be a PM in Web3 and how that's changed as crypto winter has returned, how to lead a team through ups and downs, which leaders in Web3 know all too well, including how to keep morale up and people focused when so much is changing around you. We also get into a ton of killer advice on leadership, hiring, pushing back on your CEO, working backwards, career advancement, and a lot more juicy stuff. Jason is a gem and I am really excited to share this episode with you. With that, I bring you Jason Shah.

Lenny (00:02:05):

This episode is brought to you by Coda. Coda's an all-in-one doc that combines the best documents, spreadsheets, and apps in one place. I actually use Coda every single day. It's my home base for organizing my newsletter writing. It's where I plan my content calendar, capture my research, and write the first drafts of each and every post. It's also where I curate my private knowledge repository for paid newsletter subscribers, and it's also how I manage the workflow for this very podcast. Over the years, I've seen Coda evolve from being a tool that makes teams more productive. It's one that also helps bring the best practices across the tech industry to life, with an incredibly rich collection of templates and guides in Coda Doc Gallery, including resources for many guests on this podcast, including Shreyas, Gokul, and Shishir, the CEO of Coda. Some of the best teams out there like Pinterest, Spotify, Square, and Uber use Coda to run effectively and have published their templates for anyone to use.

Lenny (00:03:03):

If you're ping-ponging between lots of documents and spreadsheets, make your life better and start using Coda. You can take advantage of a special limited time offer just for startups. Head over to to sign up and get $1,000 credit on your first statement. That's to sign up and get $1,000 in credit on your account. I'm excited to chat with my friend John Cutler from podcast sponsor, Amplitude. Hey, John.

John Cutler (00:03:36):

Hey, Lenny. Excited to be here.

Lenny (00:03:37):

John, give us a behind the scenes at Amplitude. When most people think of Amplitude, they think of product analytics, but now you're getting into experimentation and even just launched a CDP. What's the thought process there?

John Cutler (00:03:49):

Well, we've always thought of Amplitude as being about supporting the full product loop. Think collect data, inform bets, ship experiments and learn. That's the heart of growth to us. So, the big aha was seeing how many customers were using Amplitude to analyze experiments, use segments for outreach, and send data to other destinations. Experiment in CDP came out of listening to and observing our customers.

Lenny (00:04:09):

And supporting growth and learning has always been Amplitude's core focus, right?

John Cutler (00:04:14):

Yeah. So, Amplitude tries to meet customers where they are. We just launched starter templates and have a great scholarship program for startups. There's never been a more important time for growth.

Lenny (00:04:22):

Absolutely agree. Thanks for joining us, John, and head to to get started. Jason, welcome to the podcast.

Jason Shah (00:04:34):

Thanks so much, Lenny. Really excited to chat with you today.

Lenny (00:04:36):

Something listeners don't know that we know is that we actually recorded an episode between you and I back in April. It was actually my very first episode that I ever did for this podcast, and it was before I launched. It was kind of like a pre-launch launch episode, and interestingly enough, by the time the podcast launched and it was going to go out, well, let me also add that we chatted mostly about Web3, forgot that detail. So, most of our chat was about Web3 in the state of Web3 and PMing in Web3, and by the time the podcast's supposed to come out, Web3, things have changed in the world of Web3, and so, it kind of felt a little stale and out of touch, and so, we decided let's do it again. And so, how do you feel about that?

Jason Shah (00:05:15):

I appreciate that, Lenny. I'm honored that you would have me back. I'm going to count it as the personal record of two times on Lenny's Podcast, even if the world only knows it as one.

Lenny (00:05:26):

Wow. Good one. Okay, first ever guest and first two-time return guest. Amazing. Okay. To set a little context for folks on your background, your career, could you just give us a 60-second overview of your background and your career and how you got to what you're doing today?

Jason Shah (00:05:45):

Yeah, for sure. Thanks again for having me, Lenny. So, my career has all been about solving important problems in a unique way. I think the latter part is the youngest child in me who has to be special and do things different than other people, and the former is about making sure that my time is spent well since we're all limited there. So, I actually got started in a sense in tech when I was 15. I started my first company, much like a lot of teenagers, it was around test prep and getting people ready for college, and it was my first exposure to using technology at scale to help people, and I just found it addictive ever since.

Jason Shah (00:06:20):

And so, I ran that company for seven years through school, was lucky to do a small acquisition to a partner of ours that we had worked with throughout, and then I would just hooked, and I moved to San Francisco without a job. I was really arrogant. I said, "I'll never work for anybody else," and then lo and behold, Yammer comes along, I'm super excited about it, I had been working on a product actually in the same space. And so, that was actually my first formal product management role, and I stayed at Yammer, I stayed through the Microsoft acquisition back in 2012. Low and behold, I was at the world's largest productivity company at Microsoft, and most people there in my opinion were wildly unproductive and I wasn't shipping a lot. I got the itch again, so started another company called and ran that for about four years, and then eventually, we found a better fit with Amazon. They were growing their AWS offering, SAS products. So, we partnered with them to kind of do a small acqui-hire and help build the team out and the product there for a little over a year.

Jason Shah (00:07:18):

And then again, to be honest, I got bored and excited about what Airbnb was doing and the mission around belonging. That's why I was lucky to meet you and so many other really wonderful product leaders and just human beings in general at their core, and then to keep things brief for now, I got to work on a lot of really exciting products and businesses there, but eventually got the itch for Web3 after being a kind of observer from afar, investor, and I wanted to be a builder in Web3 specifically, and to me, it's a new vision of a better version of the internet. I'm really excited about that. So, I've been with Alchemy which is a blockchain infrastructure company for the last year, and really excited about all the opportunities. I've gotten to work on products that have been part of most people's everyday lives, and I'm hopeful that we'll get to do that with Web3 and Alchemy as well.

Lenny (00:08:05):

Amazing. I just realized as you're chatting there,, I'm pretty sure I used that back in the day. I think I just realized that.

Jason Shah (00:08:12):

I hope so. That would be a new, I'll add that to my second podcast achievement is if I got Lenny to use a product that I worked on, especially a startup.

Lenny (00:08:20):

Wow. Cool. Okay, so we're going to go a little bit backwards through your career and start with Web3. We're not going to spend most of the time on Web3, but just thought it'd be good to chat about some of these things, partly because you guest authored the sixth most popular post, online newsletter of all time, currently at number six, and it was about how to be a PM in Web3. Basically it's called The Product Manager's Guide to Web3. And so, a few questions there I wanted to touch on. One is just like, how would you describe the current state of Web3? We're recording this at the end of July, and so, we'll see when this comes out. But I'm just curious from someone working within it, kind of going through the boom and the busts, not the bust, the winter that we're kind of in a little bit right now. Yeah, how do you feel about it right now?

Jason Shah (00:09:01):

Yeah, for sure. So, as much as I'm a techno optimist, I'm also realist, and with that being said, I genuinely believe Web3 is in the strongest position that it's ever been in. I think it's important to remember that the term Web3 has barely existed in kind of popular lexicon for barely a year. We've definitely had crypto for more than a decade now as technology, arguably as a financial instrument of some sort, but specifically the number of companies that I'm seeing be formed, the number of products that are starting to actually achieve some form of early product market fit, some products that are starting to scale. There's definitely been obviously a huge drop in price. There's definitely been some huge scandals in terms of financial mismanagement and the contagion from that.

Jason Shah (00:09:46):

But I think it's been my experience that a lot of new technologies don't move up in a straight line, and Web3 is especially challenging here because so many things have been financialized from the outset, whereas generally speaking, you'll see startups or new technologies mature over many years, whether it's the internet itself, artificial intelligence, QR codes, all sorts of things that kind of have gone through different periods of adoption, and so, I think we're seeing things kind of record Ethereum transactions happening, new Layer 2 technologies launching all the time that are going to help scale Layer 1 Blockchains, Solana has announced its phone that's going to be the first sort of Web3 native phone out there. So, there's so many new exciting product developments and users entering the space that as much as prices have come down, I'm really optimistic about the state of Web3.

Lenny (00:10:32):

I think about a little bit is going through this shift in excitement about Web3 as a PM within a company working in this space, I imagine it tests some of the core skills of a PM, like keeping people focused, prioritizing effectively, keeping morale up. If people are getting like, "Oh man, all my cryptos going down," I'm curious how you've been able to leverage those skills and what you've learned going through this experience, keeping people focused, morale up, prioritizing effectively, those sorts of things.

Jason Shah (00:11:00):

Yeah, it's a great question. It's really important, right, because we've seen in this space that there are these cycles, and I think that morale and ability to keep building are the determinants of long-term success, and if everybody kind of takes the ball and goes home, that uncertain future won't necessarily materialize. So, in my opinion, I think that the only way to maintain moral is to make progress. I think that no speech, no sort of extrinsic motivators like we're going to give everybody some free crypto to keep motivated about it or something like that really works. I think people get really excited when they see progress.

Jason Shah (00:11:37):

So, for example, at Alchemy, we see more developers than we've ever had on the platform today, and then we're shipping, we just launched Solana support and people are like, "This is real." We're actually doing things, building things. We just had our team out at EthCC which is a big conference in Paris for the Ethereum community, and it was wild the number of people that were there, products being built. Pretty much every crypto conference has a hackathon, and so, it keeps the spirit of building so alive.

Jason Shah (00:12:03):

And so, I think it at Alchemy and just in other situations that I've been in as a leader over time, I think it's all about a focus on progress and moving forward. We saw this at Airbnb when the business had a draw down in revenue, and I know you'd covered this with Sanchan recently, right? It was 85, 90% revenue and you didn't know when it was going to turn around, right? It's not just like, "Oh yeah, this will come back in six months and we can just keep plowing forward." But I think what worked was making progress and actually focusing on product and your customers, and ultimately if you hire the right people who are motivated for the right reasons, I think that recipe keeps people highly motivated and highly effective at building for when things do eventually turn around.

Lenny (00:12:44):

One of the most interesting and maybe surprising points you made in the post that you wrote about being a PM in Web3 is that there's much less need for a PM, especially early stage Web3, and it feels like, the stuff you're talking about feels like a PM's really helpful along these lines. So, I'm curious, are things changing at all there? Have you changed your perspective on PMs and Web3, and then I don't know, where do you see the evolution of product management and Web3?

Jason Shah (00:13:09):

I actually am seeing things change a lot, and one thing in Web3, if one learns nothing is the ability to admit when they're wrong or when things change. And so, I think that that's exactly what I'm seeing. So, basically, I'm specifically noticing a lot of teams hiring product leaders, more product managers. Those product managers are actually now working kind of increasingly in sort of more traditional product management fashion, in addition to some of the differences that we discussed in the post around the community management and role in marketing and things like this, but specifically, Uniswap just made a big hire out of Meta. I saw that Gemini also did the same. We're seeing OpenSea hire a lot of talent along these lines too, even through the ups and downs that their business has seen, and at all levels. Whether it's kind of product manager, senior product manager, director, VP or CPO, you're seeing it across the board.

Jason Shah (00:14:03):

And so, I think that's partially happening because you're seeing a maturation of products, right, and so, maybe you can start early with a few engineers, a community manager, get the ball rolling, but eventually the product is more mature, the complexity has grown, the role of the product manager is far more useful than they can differentiate. I also think the market is getting increasingly competitive. So, there's many NFT marketplaces. There's many Layer 1 and Layer 2 blockchains. As a result, I think product is always a competitive advantage, right? If it's working, it improves strategy, it improves execution, and improves team collaboration. And so, maybe that was less of a difference maker before where these teams didn't need that competitive advantage as much because maybe they launched a token and the token was mooning, and so a bunch of people were adopting the product, but that only lasts so long, and first principles still come come in to focus, whether it's one day or one month from now.

Jason Shah (00:15:00):

So, I'm definitely seeing it shift. It's definitely making a huge, positive difference in the cases that I've observed, and my hunch is we're only going to continue to observe this because with more user adoption comes new challenges, and for all these players that are growing and getting some form of adoption, the product complexity is only going to grow, and having somebody to help lead teams, help prioritize between all the different products that they could build or strategies they could pursue is going to only increase in importance.

Lenny (00:15:27):

I know we're like we're PM people talking about the value of PM, but something I find is that people that are kind of anti having a PM or don't see why they need a PM in my experience just haven't worked with a great product manager because my experience, you find a great PM, they just make everything better, and so, it's not surprising to hear what you're sharing which is people are kind of discovering that value of bringing on a product manager, even if it's mostly engineering work. And so, that's promising, and I wonder if that's just a natural evolution of a new space where people are like, "Eh, I don't need PMs in this one," and then like, "Oh, okay, well, I see. All these things aren't happening. We need someone to help. Who can do that for us? Maybe it's a PM."

Jason Shah (00:16:06):

Yeah, that's a great observation. I think that combination of having a direct need for something that emerges as well as if somebody's had either a bad experience or not even had any experience with somebody who can play this role which is quite common in Web3, especially because a lot of folks are relatively early in their career, given the kind of accessibility of the space, and I think frankly the more adept understanding of the space naturally that a lot of people have when they're early in their career and less set in their ways. And so, that's a great point, and as a result, the better PMs we see in Web3, hopefully the value will prove itself out over time.

Lenny (00:16:41):

And hopefully they do well so people don't keep getting burned out by bad PMs.

Jason Shah (00:16:45):

We're rooting for all PMs, but definitely Web3 PMs too.

Lenny (00:16:49):

Yeah. What's surprised you most about working in Web3 as a PM?

Jason Shah (00:16:53):

I mean, I think that the biggest surprise to me, despite what we were just talking about, was how big some products have gotten without kind of the traditional either product manager role or without the playbooks that we're so used to from the last 20 years of the internet. And so, for example, Uniswap has done more daily volume on certain days than Coinbase, and Uniswap is about a hundred people versus 5,000-plus at Coinbase, right? So, that's astounding to me.

Jason Shah (00:17:21):

I think a lot of these NFT collections and communities that have grown. I met with a lot of these at NFT.NYC recently, and a lot of them, aside from the price speculation and things like this, have actually built, the Bored Ape Yacht Club is actually building a metaverse project that does look better than some of the digital games that I've used in the past of Second Life and things like this. Obviously, a lot of time has passed and so there's a greater foundation of technology to build off of and they're working with a partner on that product as well, but there's a ton of progress being made without some of the traditional product structure or individuals. And so, again, I think PMs play a really strong role, but it's been incredibly surprising to see how far products can get without the product playbooks and resources that somebody who's worked in the internet space from the last 10 or 20 years is so used to.

Lenny (00:18:11):

Awesome. Okay. We're going to move on from Web3 and chat a bit about some of your other career accomplishments and companies you've worked at. So, you worked at, you mentioned Yammer, Microsoft, Amazon, Airbnb. I'm curious which of those companies has most informed the way you approach product and build product and run teams because they're all so different in how they operate, and I'm always curious what company is the formative experience for you that's like, "Here's how I like to build product most." I know it's always a combination, but how do you think about that?

Jason Shah (00:18:39):

Yeah, it's definitely a combination, but I would say if I had to pick, Amazon, even though I was only there for about a year after the acquisition. I say that because of this blend between product and business thinking that is especially present there. And so, people say Google is an engineering culture. People said Facebook is a product culture, Airbnb or Pinterest, sometimes a design culture or things like this, and I think that Amazon was a place where you couldn't divorce business and product. You couldn't be a product manager without thinking about revenue growth, without thinking about go to market, and I really like that because as a startup founder doing product in a bigger company, it gave me the chance to exercise a lot of those skills.

Jason Shah (00:19:24):

It's very similar actually to how I feel at Alchemy now where I remember my first month there I was like, people ask me how's it going, I'm like, "I feel like an athlete. I feel alive again." I can do M&A one day, I can be doing product another minute. I could be figuring out, oh, we need to hire our first lawyer to write onboarding plans for employees the next minute, and it wasn't as siloed as sometimes a product role can be. So, I think Amazon, I went there to learn and understand. That was my biggest goal was this is an incredible company that's gone into... The Whole Foods acquisition happened when I was there, and I was wondering how does the same company kind of within retail win with the AWS, go create studios, and I think the Amazon culture ultimately more than anything else around ownership, being vocally self-critical is right a lot as one of the leadership principles. All these things combined I think created a really unique culture.

Jason Shah (00:20:12):

So, I would say Amazon's had the biggest impact on me, and there have been certain lessons that I've taken from, like you said, all these places, but Amazon was by far the place that I think left the biggest mark on my view on product and leadership.

Lenny (00:20:26):

That's quite amazing that you were there for a year and that's the one that's most informed and impacted you. Do you feel like people should try to go work at Amazon as a training ground as a PM? Is that something you encourage PM to try to do?

Jason Shah (00:20:37):

In general, I certainly had a positive experience, but I think that as you know and as I'm sure you've advised countless people, it's so context dependent. Are you learning the zero to one? Are you learning the one to scale? What's your aspiration? Is somebody trying to start a company eventually, or are they trying to work the ranks of the product leadership trajectory? And so, I definitely enjoyed it a lot, and I think to your point, there's often a non-linear sort of correlation between factors that we traditionally think are linked, right? So, my time there was one of the shortest, but my learnings were some of the greatest because I was really intentional and maybe because of the sort of moment in time and what I wanted to get out of it.

Jason Shah (00:21:17):

The same way for what it's worth, while we're talking about this disconnect, when I went to Yammer, I also interviewed with kind of... This was the era of TaskRabbit. I talked to Square and I remember people always say, "Well, what stage do you want to join seed, Series A, Series B?" And the crazy thing is that Yammer was, it was already passed a hundred people, it grew to 500 by the time of the acquisition, and it felt almost like the culture was so tightknit, it felt like a seed stage company at some points, even though eventually it kind of felt like... Well, once it was acquired from Microsoft, we'll just say it didn't feel like a seed stage company anymore, but it felt smaller than a lot of the actual smaller companies than I was at. So, I think that's something I've noticed a lot is that a lot of the proxies don't necessarily match the internal realities in certain cases.

Lenny (00:22:01):

You mentioned you picked up a bunch of tactics and kind of lessons from some of these companies. What's one concrete process or tactic that you took it away from either Amazon or one of these other companies that stuck with you that you like to kind of share with folks?

Jason Shah (00:22:14):

Yeah, definitely. I mean, I think one that Amazon is well-known for is the working backwards process, and for those that don't know, the idea is try to define effectively an ideal end state which funnily enough is very similar to some of what we both experienced at Airbnb and took away, and usually the mechanism for doing this is what's called a PRFAQ, and that's a press release and frequently asked questions, and it forces a certain degree of clarity to have to actually write a press release about the product that you're going to eventually launch.

Jason Shah (00:22:44):

Every employee goes through actually like a business writing class after they start at Amazon. They give you a little card with five tips that you're supposed to keep on your desk about concision and specificity in the words you use. For example, you should never write the word great in an Amazon press release. You should write user friendly in X, Y, Z way and will save customers time 20 minutes each day through this. It's intended to be very concrete in a way that avoids some of the fluffiness that frankly... It's funny, when people try to move from slides to docs, they really just import the same mindsets that they use in slides, but just with more words now.

Jason Shah (00:23:22):

And so, I think the working backwards process of establishing the long-term goal using a mechanism like a press release and the FAQs where every word matters, and even the FAQs, for what it's worth, there's a section for external FAQs that you would include for example as an appendix, but also internal FAQs that are meant to de-risk launch or raise the elephant in the room or dogs not barking as Amazon likes to call it often. So, that was a really helpful process that felt very true to me as a way I like to live my life as well, and then also very applicable.

Lenny (00:23:55):

The tidbit about not using the word great is so interesting. Is there anything else there that you could share about just basically just like how to write effectively and communicate and launch. Is there any other tidbits along those lines?

Jason Shah (00:24:07):

Yeah, that's a good question. In addition to not using the word great and words like it that are either subjective in what they mean or unclear in what they actually mean, definitely using numbers more than adjectives. Strict concision, I would go over these documents countless times, and there's a phrase, I can't remember, it's either Mark Twain or another famous writer who said kill your darlings, right? Cut, cut, cut, and just remove. And so, I think I found that really useful in emails I write or documents I write to this day is just going over, not because you're saving ink by cutting words, but because it forces clarity of thought. Fewer words means every word is 10 pounds in weight instead of one, and that means that the decisions you're making, the trade offs are far more intentional, and in the case of great, if you say something is great because we're going to deliver something in two hours versus Amazon's great because the selection is very wide, the implications on strategy are completely different. And so, that's one of the benefits of being very specific and very concrete in language.

Lenny (00:25:12):

I didn't intend to go too deep into this topic, but no one's ever covered this working backwards process on this podcast, so it's kind of interesting to talk about it a little bit more maybe. How does that actually work? So, you sit there and you actually write out a press release that would go out when you launch this thing. Is there like a template used? Is there anything you could share for folks that want to try this out and/or point them to a resource that will help them down this road?

Jason Shah (00:25:36):

Yeah, definitely. That's a great question. So, there definitely is a template, and so, it's a combination of an internal training where you have to write one of these documents. You review kind of good, bad, medium versions of this. It's generally used if there's let's say a proposal for a new product or even a proposal to buy a company. This helps really simulate what it's going to be like.

Jason Shah (00:25:56):

With respect to a template, what I recall is it was often sort of an introduction where you get kind of right to the point. You say what you're announcing. Then usually you would describe the problem in one paragraph and in very clear language. Again, all of the writing is this way. Then the solution, you briefly describe the product. After that, there's always a customer quote, and this is an example of this customer obsession that Amazon is so famous for that many companies like to say or emulate, but I think it really kind of may not be true if you evaluate the mechanisms that they use, for example, product specs that either don't have customer data or don't have quotes from customers, things like this. And so, there's a customer quote, and you have to literally put yourself into the shoes of... Let's say you were launching Prime. Put yourself in the shoes of Lenny from San Francisco. What exactly is he going to say when he has access to this, and how's it different than his life today, and what are the words that he's going to use?

Lenny (00:26:52):

You can't use great.

Jason Shah (00:26:53):

I mean, if great is one of your favorite words, maybe you could stretch it, but I think if you were in a room with your peers at Amazon, they might put some red pen through any greats that are used there. So, I found that really helpful, and it also helps force out of this box that product managers, product leaders tend to get into of thinking that they are always the customer and being a little sort of intellectually lazy, where I'm like, "Yeah, I would like Prime, so let me write the quote for what I would like," but maybe I'm only a small segment within our total customer addressable market.

Jason Shah (00:27:26):

So, anyhow, there's a customer quote, then there's one leadership quote similarly that this achieves a complimentary goal, like how does this fit into our strategy in a way that you would express to the public but is still true to what the internal sensitivities and mechanisms would be. And then a call to action towards the end, and not just download here, but this will be available to customers next month. They can go access these portals within these Whole Food stores at this state. It again forces clarity of thought with respect to not only the rollout plan, but taking a step back. When you read it, do you feel like you would actually want this product? Would you use it? So, I found that really helpful as a structure.

Lenny (00:28:05):

Can you just summarize those again real quick?

Jason Shah (00:28:07):

For sure. So the structure of the PRFAQ docs was generally an introduction where you're announced the product, problem, solution, customer quote, leadership quote, and a call to action.

Lenny (00:28:17):

So, interesting how similar that is to a one pager potentially. The other thought I had while you're chatting, so the Airbnb approach is work back from the ideal, Brian talks about it, the 11-star experience versus the Amazon approach which it doesn't need to be the ideal, it just needs to be an awesome launch. So, that's an interesting difference, both effective in different ways.

Jason Shah (00:28:37):

I think people tend to, when they see that both companies have some sort of working backwards process of thought, I would say working backwards on one hand and then 11-star experience on the other. Listening to how you describe it, I want to almost frame it as working backwards from sort of a moment in time or a launch like you said with Amazon versus working backwards from a quality standard in some sense of an 11-star experience.

Lenny (00:28:59):

Going in a slightly different direction, one of the things I wanted to chat about is you worked at all these different companies and they have different types of leadership and different approaches to leadership. And so, I'm curious, what have you learned about effective leadership watching all these awesome operators work, and what kind of separates them in your experience from folks that maybe aren't as effective?

Jason Shah (00:29:18):

Yeah, it's a great question, and to briefly recap, right, I've gotten to see somebody like David Sachs who've been the CEO of PayPal and then the founder of Yammer and gone to do many more things since then. I've gotten to see sort of Jeff Bezos at a distance. I was never that close to him obviously and never got to work with him, but got to observe his impact on the organization. Obviously, I've gotten to witness Brian Chesky and his leadership in sort of the pre-IPO days as well as through the ups and downs of COVID, and then also now at Alchemy, our co-founders, Joe and Nikil are leaders that have really had an impact on me as well, and I would count myself, but I've also see myself as a bad leader in the start of [inaudible 00:29:56] and learn from that.

Jason Shah (00:29:57):

I think it's a really important thing to reflect on, and I think for me there are three things that have stood out the most. I think number one, nothing is above them. I've seen whether it's Brian caring about the full bleed image on the homepage, whether it's Jeff Bezos who famously would receive customer emails, read many of them, forward them, and he's famous for question mark emails where for his time's sake he would just forward an email to a leader with a question mark and you would just have to figure it out and then report back in 24 hours with the resolution thereof. But nothing's above them, and a lot of founders or a lot of CEOs or even CPOs and leaders think you get to a certain point and then I'm above a product spec, I'm above looking at the data running a sequel query, and I think that that is a mistake in a lot of ways, especially from a standpoint of who people come to respect as well as efficacy at one's job.

Jason Shah (00:30:51):

And then the other two things would be, I think they're in the details. So, it's less about being above something, but this is kind of Amazon's famous for auditing the details for example, and leaders are... For example, when we were going to launch Prime, order a bunch of Prime things and see what happens and really test things out, and write up a long feedback email on Saturday or something like that, and make sure that things are moving forward.

Jason Shah (00:31:12):

So, I think in my opinion, some of the best leaders, David Sachs would do this too. He actually ran the product reviews. It was the CEO of the company doing product reviews, not some kind of middle tier of a director of product who was just running them. They were force involved and there were things to delegate and activate around, but Sachs was in all of those details and ran those product reviews himself and would talk to the product managers directly, and I think that was really impactful, and it also, I think from an accountability and culture perspective, when you're PM and you talk to the CEO and you feel like you're presenting something at product review, it's totally different, and it creates a certain amount of responsibility and quality, frankly, that I think is really important, and it's a way to coach obviously as well for those leaders to really make a mark on the organization.

Jason Shah (00:31:59):

And then lastly, I think they adapt, right? I think that are a lot of leaders who are like, "I've worked 20 years to become a leader in this way and I have a playbook," either based on past experience or based on some sort of philosophy that they've developed over time that they feel committed to in some way, and I think coming back to some of these examples of watching Brian lead through COVID or watching Joe and Nikil now through this particular crypto winter shift gears and figure out exactly like we're still building the core business, but how else can we lean into this and adapt to the unique opportunities that are in front of us. I think that's really powerful. So, what I've seen is nothing is above them, they're in the details, and they adapt to new information and new situations. That's what I've seen the most that I've appreciated in the best leaders that I've gotten to either observe or work closely with.

Lenny (00:32:46):

Awesome. That's super interesting. The first two are kind of connected which is really interesting, and it just reminds me of Brian and how detail-oriented he was about everything. He used to review every product launch and every screen of every new product. We had to show him here's what we're launching this week, and he just kind of went through and either blew it up or let it pass. And then I just remember the founders, when they were designing the office space, just looking at pictures of listings they wanted to... Because Airbnb, the office conference rooms were modeled after Airbnb listings, and Jim just looking through hundreds of listings that the team brought him and he'd just picked the ones that he wanted to turn into conference rooms. Also, obviously Steve Jobs. This is a really interesting through line of great leaders is just this huge attention to detail, and there's probably something about once they let go that thing start to kind of diminish. Is that what you find?

Jason Shah (00:33:39):

Yeah, that's such a great point. You mentioned the Jobs example and there's a great book that you've probably read or in your community seen, I believe it's called Creative Selection by Ken Kocienda about the early days of the iPhone, and I think it was Project Purple or something like that, and you're absolutely right. There wasn't no slides, none of this. They brought in the prototypes for each of those reviews and things like how to do typing on a tiny screen and those early keyboards and how to do auto complete, and Jobs was totally in those details from Ken's telling in this book.

Jason Shah (00:34:10):

So, I couldn't agree with you more, and it's something that people miss because most of their exposure to leaders is on a YouTube video or at all hands, and so, they don't really get to see that side of leaders I think, and it's also not what I think from an ego perspective is kind of what people want it to be about. They want to be about making big decisions or commanding a large group of people, and I think it's hard to do that without these pieces.

Jason Shah (00:34:34):

One other thing I just wanted to briefly touch on to your point on how they're connected, it's a really good point, and at the surface it almost seems like they could potentially be the same thing. One thing worth calling out though I think is the idea of something not being above somebody or a person not being above things. I think the biggest thing I take away from that is humility is that nothing is not my job, right? Anything, could be picking up paper off the floor and putting it in the trash, or it could be reviewing a product spec, whatever it is, and then begin the details in my opinion is about craft, right, and really understanding things at a low level such that you're able to reason about it and make good decisions, like Brian with the homepage or Bezos in some cases with customer processes that he got in the weeds on. I think the two together, humility and being excellent at craft, I think is a very potent combination, especially when you throw in the last thing of being able to adapt to any situation.

Lenny (00:35:29):

That's really interesting. What it also makes me think about is the reason things are less good often if there isn't a person at the top that's being very detail-oriented, and I find this with the newsletter and this podcast and other stuff is no one's going to care as much about it. No one's going to be like, "Oh my god, I really need to get this right so much because I'm just like, I'm personally feeling responsible for the quality of this stuff and it's like it's on my shoulders to make this awesome." And so, I think that's probably why a lot of the best stuff is led by a singular leader or singular opinion or singular person. A lot of the best startups are just someone's vision is like, "Here, this is what we're going to do," and then the more it becomes a community-driven thing, the less often it ends up being successful.

Lenny (00:36:16):

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Jason Shah (00:37:19):

I feel like you're totally right, especially, I mean this is the natural progression, but it doesn't have to be that way right? And I think to your point, I think a lot of leaders focus on accountability in an organization once they get large, and so, you see things like performance reviews and things like this. It's a very top-down approach to trying to drive results, but is opposed to a sense of accountability if you drove a sense of responsibility. If people felt like this is my company too, this is my product, this is my office floor. I don't want trash on the floor. I'm going to pick it up and throw it there. Even if we have somebody whose job it supposedly is to clean that up, it's like I take pride of ownership in this and I'm connected to it, and I think that makes all the difference in terms of... At Airbnb, I think people who felt that way were willing to push back on certain things, or they're willing to propose new ideas because they felt invested in the company.

Jason Shah (00:38:12):

I see it at Alchemy all the time. I see an engineer hop in and fix something at 3:00 AM because they feel committed to the code base, and it's not a thousand-person engineering organization where my only job is to make the iOS app 2% more effective at engaging users.

Lenny (00:38:27):

So, you touched on the skill of pushing back on a founder or CEO, and I know that's something you're really good at. I've seen you do this. I'm curious what you've learned about how to effectively do that as a PM at a company pushing back on a CEO or founder when you disagree.

Jason Shah (00:38:40):

I mean, I think this is one of... I actually think it's one of the most misunderstood terms in a sense because I think language like we were talking about earlier is so important, and yet what you call something ends up defining I think 90% of what people understand about a concept, right? And so, pushback is, I couldn't imagine a word more viscerally that makes you feel like you're sort physically going against what somebody else wants, and it gears people into a mindset of then, well, how should I push back. It starts from a place of I need to disagree, I need to say no. It's a very negative mindset, purely based on the word that has come to label a behavior that alternatively could be about how do I shift the direction on something, or how do I help the business actually succeed when I disagree with somebody about something, and that's a very different mindset.

Jason Shah (00:39:34):

And so, the two things that I've seen be most successful would be, I think number one is actually understanding what a goal is or what somebody's kind of issue is with something, and then actually aligning those things in some way. So, in coming back to Airbnb, I remember Airbnb had bought a company, Luxury Retreats. There was a goal to integrate that business and that product into the full Airbnb suite, and there was a lot of potential with that, but I remember that there was part of the product experience that was oriented around chatting with somebody and the idea that the business had had a very large team of wonderful people who helped you as concierges basically for your trip, and so, this was a team that I was on that, to be honest, had fairly low morale. It's always difficult to integrate an acquisition with a company, especially when we were based in different places, et cetera.

Jason Shah (00:40:26):

I remember hearing from a leader who had been at Airbnb for a while who's very effective at persuading senior leadership, and they understood why this was a problem because this chat product was growing in complexity. You'd have to build all these features into it, and nobody could successfully shift the direction, and as a result, it was just this... It was a mess as a result, and there was very low morale because we were taking on too much scope, people weren't sure it was the right product, it was being built up as one giant launch as opposed to an iterative thing. And what was really interesting was that this leader was very effective at understanding that the goal wasn't about building a bunch of features. It was about, as often discussed at Airbnb, a magical experience.

Jason Shah (00:41:06):

And so, when we took a step back, it was reimagined as trip designers, not concierges, and their goal was to design your trip, and part of that meant a very elegant, simple chat experience so that you could have a efficient, fast, positive experience with that trip designer and move on. And it shifted the pushback of like, "We can't build this thing, it's too many features, we don't have enough time, we don't have enough resources" to, "Oh, we all want a really elegant, really smooth, slick experience for our customers. How do we do that? What's a trip design or a new concept that is actually going to elevate things? We're not telling you we want a payback scope. We're not saying we want to settle for less. We're actually just not only going to call it something different, but also envision a simpler experience which is more elegant. It's more on brand with luxury."

Jason Shah (00:41:51):

Boom, all of a sudden, everybody gets what they want. It's a better customer experience, less scope, and it wasn't about saying no. It was about understanding what we're all actually sharing as a goal which was a great simple customer experience and then actually building that. So, I saw that to be really effective and I think that that's something I try to bring into my career. I have a couple other examples if it's useful, but that was a big one that I learned from Airbnb.

Lenny (00:42:16):

Yeah, another example would be great. One thought there though is do you think it was mostly the name and the concept or was it that it was a bigger idea? What do you think it was about reframing it that way that got people, "Oh wow, okay, now I'm really excited about it again"?

Jason Shah (00:42:30):

That's a great point. I think it was a big idea, right, with a good reframing, and I think it's like many things where there's the substance of something and then there's the communication of it. And so, this is true often, for example, if a company is changing strategy. Oftentimes people might walk away feeling like, "Yeah, I guess I kind of agree with the strategy, but the way was communicated was really poor," or vice versa, like, "Yeah, they told us in advance and they sat us down all hands, but I really disagree with this strategy and I'm going to be dug into my heels and not disagree and commit now."

Jason Shah (00:42:58):

So, in this case, I think you're totally right. If it was just window dressing of... Founders are too smart, especially at all these companies we've talked about, to be fooled with a simple renaming of something. But I think the combination of a bigger idea, more exciting idea that was at the heart of what we were all going after together, combined with a simple way of communicating it because I've also seen big ideas that are poorly communicated fall flat on their face and not achieve the intended outcome. Those two together, I think were a really potent combination.

Lenny (00:43:28):

Awesome. I'd love to hear another example.

Jason Shah (00:43:30):

Yeah, for sure. So, a recent example at Alchemy actually, right? We're growing, we're hiring, but there are a lot of roles, especially being in Web3 that are not yet created. For example, there's traditionally growth, product growth marketing, we've created new area around growth operations which I'd be happy to talk about if we want to get into it. But it's a really interest interesting area, and we were going back and forth on should we hire for this role, it's not even a real thing. We've looked at some candidates, we're not so sure about them. And when I realize with our founders who are incredibly smart, very talented, have built the company over so many years now, they want to win. That's what they care about at the end of the day. They are so driven to win at the end of the day.

Jason Shah (00:44:10):

And so, ultimately, it wasn't like, "Let me make some rational argument about the role of growth operations or let me defend some issues with this person's resume that maybe you're spotting when we make this hiring decision," but, "Oh, you want to win? Oh, we want to grow faster? Awesome. This is the way to do it, and that's how we're going to actually become the generational company we want to be." Again, a reframing in this case around, yeah, we might disagree or squabble about certain things at a detail level, but I understand what we all came here to do and let's focus on that and how this is a part of that versus just focusing on maybe the means to an end versus the end itself, and the end always brings a lot of clarity in my experience.

Lenny (00:44:49):

What's cool about both these examples, and another guest touched on this, when you're trying to influence the CEO or the founder, coming back to your working backwards concept, you almost want to work backwards from what are they excited about, how do they see the world, what's important to them, and then pitch it that way. So, in the first example, I imagine they were pitching to Brian and he's like, "Yeah, drip design, that sounds like something Brian would love." Then in the second example, "Yeah, we're going to win. Here's how we win." So, that's a really interesting takeaway there.

Jason Shah (00:45:15):

I mean, I think we all forget that we're all just humans, and at the end of the day, we all are busy, et cetera. It reminds me of a lot of sales, right? I was very unsuccessful when I was trying to do outbound sales in the early days of my last startup because I didn't understand this. I'm a product person. I'm not a sales person. I didn't listen to what people cared about. I didn't kind of work backwards from what a CRO or head of people that we might have been selling to cared about. I was just about features and here's what we can do for you and this and that. But all they cared about were one or two things, right? Maybe the CRO's growing revenue. Maybe the head of peoples worried about culture or scaling their talent organization, and we were nowhere near that list.

Jason Shah (00:45:56):

And so, I think it's similar for CEOs, and there's a huge disconnect when say a PM walks into a meeting with the CEO and they're talking about something that CEO is 10 miles away from thinking about, and certainly even the mindset that they're bringing to the conversation is totally different. I think Casey made a lot of great points about this in the recent podcast as well.

Lenny (00:46:16):

Sweet. Casey Winters, podcast plug. Okay, so something else that you're really good at is you don't kind of focus career-wise on working your way up the ladder and being like the top PM, and you seem to be really good at kind of following with what's interesting to you and your interest and your curiosity. Is there something that you've learned there, something you could share for folks that are just like, "Oh my gosh, should I just keep in with this job and work my way up? Should I try something new?" What have you learned about that sort of thinking?

Jason Shah (00:46:46):

There's the framework I like is ladder versus map, and I think that you can be either person that any point in your life. Sometimes there's a bit of a set mindset that somebody might have one way or another, but I like ladder versus map. Ladder is about moving up. It's more influence, more power, a higher title, things like this, whereas map is I just want to go wherever's interesting, right? I literally think of it, I think of my career very similar to travel. I want to go to Greece. I want to be hungry, walking around in India, sweating in a hundred degree weather. I want to go to Australia and kind of get locked out of my hotel and see what that's like.

Jason Shah (00:47:23):

I'm okay with discomfort because it's interesting. Sometimes, for better or worse, maybe this is a privilege, it's certainly a privileged thing to say, but I care more about living a really interesting life than let's say a good or comfortable life. I think that's where the growth comes from. That's where the stories come from. That's to me the things that I'll remember the most.

Jason Shah (00:47:42):

And so, when I think about product and I'm on my deathbed, I'm going to care about the products I built and how they affected people. Nobody's really going to be looking at my LinkedIn, hopefully for their sake and mine, at my funeral. Sorry, it's a very morbid analogy, but I think thinking of the future provides a lot of clarity about what am I going to care about a long time from now, and I think that applies to all facets of life. That's how I thought about my life partner. That's how I think about my career. That's how I think about where I want to live, San Francisco. San Francisco, a lot of people like to talk negatively about it, but I believe in the community. I believe in the place I'm interested in the long term, even if you know the short term it has some challenges to it.

Jason Shah (00:48:21):

So, I personally believe really strongly in this kind of ladder versus map distinction, and I think a lot of people are very intentional in the micro. They think about their next job, their next title, how much salary and equity there is. In good ways too, they think about the team that they're going to work on next with, but they're very unintentional about the macro. What's the big picture? What do I care about as an individual? There's not a lot of classes for that. There's not a lot of blog posts in the product management field about the touchy-feely side of this, and who are you as a person, where do you get energy from. So, for me, I found that really clarifying and it makes career decisions that have seemed risky to other people seem inevitable to me.

Lenny (00:49:03):

Is there a story of or example of how you use this approach to make a decision at where you end up going, and/or or is there something that you maybe regret or are really happy with in terms of the kind of the fork in the road, looking back, using this way of thinking?

Jason Shah (00:49:18):

A few concrete examples, actually. I'll keep them brief though. One is when I first moved to San Francisco, and I had mentioned I did a small sale of that education company, and I could have done a lot of more productive things with my career in the short term. I had all my peers from college who had gone off to their great jobs at Google or whatever. I said, "I'm looking to move to San Francisco and work at my dining table, and I have a little bit of savings from this, so why not? Let's see. It's going to be super interesting." I mean, it was also very boring at times, and so, I didn't want a lot on the sort of micro level, but I built five or six products. I became much better at programming as a result.

Jason Shah (00:49:56):

I remember one time, it's kind of a goofy story, but I was working at my dining table, and I saw Ron Conway on the street. I was disheveled because I was just working from my apartment and I wanted to go pitch Ron Conway on this terrible idea for a startup, and so went out there, and maybe it was fortunate to not shove me to the side, and he listened to me for a minute and then I emailed him after. These are random things that happen that over time I think make us who we are. Are you the sort of person who's going to hustle and do that? When I was building that education company, I went and put flyers in people's cars in various high schools, and I was trying to get things started, and coming back to leadership, that would be below most people. It's like, "Wait, you own a company and you're sticking flyers in people's windshields?" It was like, "What's wrong with you?"

Jason Shah (00:50:40):

So, anyway, I think that was an example of time where it was like, "Okay, if I'm on the ladder," I'm like, "I got to get the best entry-level job or whatever." Even if I had been an entrepreneur before that, I would've thought about my structure in my career, and I was more like, "This is going to be interesting. I'll figure it out. I believe in myself enough that I'll figure it out." So, I did that. Yammer and leaving Yammer was similar where I could have stayed. My equity was finally worth something. I could have learned a lot even I'm sure from the Microsoft structure, but I was bored and I had been talking to a couple angel investors who were willing to put money into whatever the thing was going to be, and I felt like raising money's actually going to be really hard for me. This is going to make my life a lot easier and I can focus on product and so on and so forth.

Jason Shah (00:51:25):

That was a really hard four years. Things like an M&A offer falling through the day before your wedding, or chewing glass and submitting to the Apple iStore and being a featured app and then resubmitting because we wanted to fix a bug, and then actually now it crashes 90% of the time. It's Memorial Day weekend and you can't get in touch with the Apple business development manager who can help you out to reapprove something. It was a really stressful four years, but using the map analogy, that's like getting lost in Croatia and having to find your way out or getting lost to to your hotel in Australia or getting bitten by a dog in Thailand, which actually did happen to me. But these are interesting experiences that I think build characters.

Jason Shah (00:52:05):

So, I'll pause there, but I think there are a lot of career decisions I've made. Do I have regrets? At times, for sure because you see what would've happened if you had joined a different company at that time and it would've been like, "Oh, I would've met so many great people. I would've worked on these products. I mean, my equity would've been worth more," whatever. But I think you only lived once, and I think that these rare experiences have been very true to me and taught me things that I wouldn't learn otherwise.

Lenny (00:52:28):

What's really cool about that analogy, ladder versus map, is a lot of times you think you're climbing a ladder and you think it's innately going to be great, and sometimes that ladder falls over and the company doesn't go anywhere and/or the job sucks, your ladder's heading to some terrible place. And what I find in my experience is anytime I try something totally new and take a risk, especially following things that give me energy, and I'm just like, "Let's just take a leap on this thing," in my experience at least, it's always led to better opportunities and much more interesting work. And so, it's kind of this get off the ladder to get on a different ladder, and sometimes you think you're on a nice ladder and it's not going to get you anywhere anyway. So, explore other ladders. So, I'm kind of picturing a Chutes and Ladders.

Jason Shah (00:53:15):


Lenny (00:53:15):

There's many ladders and you want to explore the different ladders across the map. How about that?

Jason Shah (00:53:20):

I mean, I think you're totally right, and the only brief thing I would add to the way that you put it which I think captures the essence here is I think we all have a lot of false precision about what we think a given career move is going to lead to or what it's going to be like, and we forget that a lot of career decisions are made out of maybe 10 hours cumulatively talking to a team and getting signals.

Jason Shah (00:53:44):

So, I think that that false precision sometimes gives us comfort in making certain decisions and folds us back from a bolder decision that might be better, but maybe the ladder is just hidden behind some fog if you really want that, and you can get both. Maybe you can go to the most interesting place in the world, and have the success in life and progress and so on and so forth. It's just that I think a lot of people think it's totally either/or. They think that they've already figured out the precise outcome that's going to happen, and to your point, the ladder often does fall over. If that's what all your hopes are pinned on, it's a very fragile career decision I think is really difficult to navigate.

Lenny (00:54:19):

The flip side, you also don't want to be bouncing around over and over and over. As much as I talked about how I shifted and tried new things, I'm a very serial monogamous in terms of work. My first job, I was there nine years, then a startup for a year and a half, and then Airbnb for seven years, and then what I'm doing now may be forever. And so, there's a lot of value to sticking around and kind of seeing things through. And so, I guess, I don't know if you'll have an answer to this, but do you have any wisdom on when to stick with it and keep exploring opportunities at a place you're at versus trying something new?

Jason Shah (00:54:54):

My hope is that there's a balance here in the sense that the map shouldn't give the impression of 180 countries, let's do 180 tech companies and shorten the tenure from two years down to a month, and we've just created a generation of job hoppers which is even easier because we're all on Zoom. It's a good point and I really respect people like you who have stuck it out through the ups and the downs and somebody sees seven years on paper, but I mean, seven years, I don't know. How many chapters of Airbnb, how many crises moments?

Lenny (00:55:26):

Felt like 300.

Jason Shah (00:55:27):

There you go. So, I think there's a balance, right? For example, I want to be in Web3 for more than a decade. I want to stay at Alchemy for a very long time and help build the company. So, I guess when I think of map, maybe an important way to think about it is maybe when somebody is 50 or 60 or 70 and they might choose to stop working, a lot of people when they start their career actually have 30 years to play with or 40 years or 50 if they're lucky. That's a lot of chips you can play. You could do five, 10 year rounds, right? And so, I think that in terms of sticking it out, maybe I'm biased, I think that some of the absolute sort gems, if you will, in Silicon Valley and tech are the teammates that are willing to stay around for 4, 5, 6, 7 years, and they have institutional knowledge that nobody has. They have a positive impact on the culture that is impossible if there's constant employee turnover.

Jason Shah (00:56:19):

So, to me, I think that you could simultaneously be somebody who's committed to companies, stays for a very meaningful amount of time, but zooms out and looks at their career. Actually, I think maybe this was even more, right? You're now a famous podcaster. You were a successful startup founder. You were a product leader. All these things form a map and I think a really interesting career and life, frankly, that's pretty full with a lot of really interesting milestones and learnings and networks and people that you get to interact with.

Lenny (00:56:47):

Yeah. To your point about how long a career is, when I thought about it recently, this is my fourth career. First it was an engineer, then it was a founder, then a product manager when I got to Airbnb, and now this weird thing that I do, and there's so much time to explore and try new things. I will say though, I feel like the early things you do seem really important. Airbnb for me was not early, so maybe I'm wrong, but it feels like you want to work at a company where people look at that on your resume and are like, "Oh, okay, this person's probably good." So, I feel like there's that piece you got to get right at some point.

Jason Shah (00:57:21):

Yeah, I totally agree with that. For example, I think for let's say a new grad who's thinking about a product career, and let's say on the spectrum there is maybe Goldman Sachs because that's what a lot of people are doing. They're like, "Yeah, I want to do product, but I also feel like I need this gold star or whatever." And then in between is you could join a hypergrowth company of some sort where they definitely have good product people you can learn from, but definitely still room for you to do more than what a very junior person would be assigned to be doing. And then on the other end of the spectrum is I'm going to have no job, I'm just going to completely bounce around from my own projects or just work with a new startup every two months.

Jason Shah (00:57:58):

Personally in that spectrum, I tend to be more towards the middle of that where build a track record, build a network. I mean, it's crazy. Even just this week, next week I'm seeing maybe five people that I know from my Yammer days, and to your point on formative nature, some of those people, that's how I learned how to do product. That's how I learned things like AB testing. It's how I had the first angel investors in my next company. That's how I hire. I still hire people, maybe much to their chagrin, they still get LinkedIn messages for me trying to push them for the next thing.

Jason Shah (00:58:27):

So, I totally agree that those early days are really formative, and there's maybe a balance between nobody wants to be a job hopper, but at the same time maybe there's ways to also not just be a career person who spends kind of 30 years working up the ladder or is fixated on I need to be CPO but is willing to give up a director title to go be a hustler at some startup because they really believe in it and they want to take a bet or risk in their career.

Lenny (00:58:50):

You touched on hiring, and that's something I wanted to ask you. So, you're in my Talent Collective. You're a company that's hiring, Alchemy, and I was looking at the stats recently, and you're one of the most successful companies at getting candidates to talk to you, and generally I think you're just really good at hiring. So, I'm curious what you can share with folks about hiring.

Jason Shah (00:59:10):

I appreciate that, and I get a lot of value out of meeting some really talented people from the Collective. I think hiring, it's funny, it reminds me of sort of push back in a sense of what you call it has such an impact on how people think about it. It's hiring, recruiting, but if people reframe it as the people you are going to work with every day or the people who make the company what it is, it shifts the mindset. It's like how is that not the most important thing to be thinking about as a leader or as a founder. A lot of people have benchmarks. I think maybe on the Google podcast I talk about 30%, 40% of a founder's time maybe spent on recruiting because I think deep down everybody understands that that's incredibly valuable.

Jason Shah (00:59:53):

I think that for me personally, I was reflecting ahead of the podcast on how I approach things now after different stages of hiring, and for context, for what it's worth, I've been at the zero person startup. It's just me and I'm trying to convince some Google engineer to come join us which is incredibly hard and has a low hit rate, to a place like Amazon or Airbnb where you have a large world-class recruiting organization that is effectively doing sourcing for you and setting up interviews and such things like this, and there's formal calibrations and interview panels, to a place like Alchemy where it's very sort of scrappy. We need to figure out who we even want to hire. The founders still meet with every candidate. It's a really different environment.

Jason Shah (01:00:34):

So, this is kind of the spectrum that I've seen, and I was reflecting what do I think works the best, and I like to think of it in very similar motions to a business where I think there is a marketing aspect to it, there was a sales aspect, and there is a product aspect to it. What I mean by that is that on a marketing level, I think what has a person heard about your company. Do they know anybody who works there? Do they read your LinkedIn post about things and already know that you're a known quantity before they even step in the door to interview? Are they even willing to interview based on what they know about the company? And so, I think that the marketing aspect in it, and I mean it's sort of lower case marketing in this sense of course because I think a hard sell of any sort or anything that's not authentic is probably going to fail ultimately, but it's about developing a really positive kind of brand and reputation for a company but also as an individual.

Jason Shah (01:01:26):

And then if you pass that threshold, I feel like there's a sort of a sales process, and we were talking about how bad of a salesperson I am, for example, because I didn't listen to people's pain points and understand the one or two things that were most important to them. I think similarly in this context, if they're an engineer, do they want to work in a world-class engineering organization? If they're a product person or they're just really excited about crypto and they want to find a way in, a place like Alchemy's the best place for them to learn that is how to think about it, and it's not about misdirecting on or matching whatever they say, but it's about really understanding who they are and what motivates them and what they're excited about because I'm as concerned about the kind of post-hiring step as I am the pre-hiring and want them to work out and be happy and be effective.

Jason Shah (01:02:12):

And then lastly, I think there's a product angle to it that not a lot of people think about or talk about a lot because I think the product, it's one of those rare cases where job descriptions are almost like product specs, right? They're here's what the responsibilities are, here's what we need you to do, here's the qualifications we're looking for. And what's really funny about that is that product is very iterative, but somehow we just write a job description, and then it's bait, it's done, it's posted, and nobody thinks about it again until the person's hired and then they take it down.

Jason Shah (01:02:41):

I think taking a product mindset where I meet people all the time now where I don't really know exactly what role they're necessarily going to fill, I'm not really sure about exactly their seniority, maybe they don't have a lot of experience, but maybe they would just totally be a rockstar on our product team. And looking at a product that we can mold flexibly and think of the same way if at Airbnb, if we were going to build Airbnb Plus, if we just kind of came back to the Amazon working backwards and just wrote a document and it was over, that's one thing, but we didn't do that, right? We went and actually built rooms and homes that were supposed to be Airbnb Plus, and then we iterate on it and we changed the pillows and we changed the entrance and we changed the scent that you feel when you walk in. We coach host and learned about that.

Jason Shah (01:03:22):

So, I think a product mindset on hiring and iterating on it based on the candidates you're meeting, the needs of the business. So this kind of marketing, sales, product combination has been what I've found to be really effective at getting people excited, understanding who they are and what they need, and then crafting a role that actually makes the person successful, rather than just checks a box in your recruiting software as some new headcount that was hired.

Lenny (01:03:45):

One last question before we get to our lightning round. For PMs that are listening to this maybe early in their career, what skill have you found to be most important in helping you and helping PMs in general advance in their career?

Jason Shah (01:03:59):

Yeah, this is a really important question, like the others, but I think that understanding and defining what problem matters is the most important skill that I think I've taken away, and it applies to so many things. It can apply to a specific product we're building. It can apply to what a company's mission is. I think I've found it really effective because it affects pretty much everything. It affects what we're going to build. It affects is the team motivated by what we're doing. So, specifically for example, at a place like Alchemy where, yeah, we're a developer platform, but should we build an SDK so there's abstraction that is easier for developers to use? Should we build an NFT API because we think that's a really important stack to move into and an important use case to support?

Jason Shah (01:04:45):

Well, the question is what problem are we solving? It's not this versus that just in a vacuum. It's is the problem developer experienced and we want to make things easier to develop. Is the problem that an NFT marketplace, a whole suite of them are trying to grow and need more support from us, and not understanding these problems clearly? And it goes back to my first company. It was an education company, and the problem was that low-income students didn't have access to the same resources to get into college as other students, and that guided everything. That guided the pricing model which was basically free for a long time, and then we monetize on sponsorships from colleges, right? The problem matter, whereas the problem solve was there's not a... A different problem was there's just no good college readiness program. Fine, then you focus manically on the pedagogy and the curriculum and so on and so forth, rather than say the business model and an initial product that you think can work.

Jason Shah (01:05:35):

So, that's what I've found to be the most useful, and I can give her other examples if it's helpful, but understanding what problem we're actually trying to solve and really getting crystal clear about it, I think has been incredibly useful to me and energizing as well.

Lenny (01:05:48):

It's such a good reminder, even though it's such a cliche of product managers being, "Well, what problem are we trying to solve here?" People hate that, but Michael Paul, and I mentioned this on a different podcast too, he makes this point that when you do drugs sometimes, you have these epiphanies that you come out and you're like, "Love is all you need, man." It's like, okay, yep. But it feels so right. You really feel it. The reason that it's such a cliche is because people have found it to be so true for so long that it's annoying now, but it also tells you how true it is. And so, I think it's a really good reminder of yes, it's annoying to ask that question, and people make fun of PMs for that, but that's because it's so damn important.

Jason Shah (01:06:28):

Just a brief kind of additional, what you share there, I mean, I completely agree. I think it's very true in life, right? It's like, well, what matters? And it's like, well, your health, your family, your sense of purpose. It's like nobody's unfamiliar with the answer, but like most things, it's about the application of it and about the nuance of it, and I think that's what product is ultimately sort of all about too.

Lenny (01:06:48):

Awesome. Are you ready for our lightning round where I'm just going to ask you five quick questions, tell me what comes to mind and we'll have some fun. Does that sound good?

Jason Shah (01:06:58):

That sounds great. Ready.

Lenny (01:06:59):

Okay, cool. I think I'm going to start adding music to these things. I got to figure that out. For now, no music. Okay. What book do you recommend most to other PMs?

Jason Shah (01:07:07):

The Hard Thing About Hard things.

Lenny (01:07:10):

Can you add why?

Jason Shah (01:07:11):

I think it teaches product managers to chew glass and care about outcomes the way that a CEO has to, and I think that's a really useful mindset to have.

Lenny (01:07:21):

Man, this chew glass metaphor, I don't like the sound of that.

Jason Shah (01:07:24):

I saw you cringe. I was a little worried about that.

Lenny (01:07:27):

Oh my god. What a great job we have here, chewing glass. Okay. Other than Alchemy, what's a company you recommend most to PMs to go look for new gigs if they're looking around?

Jason Shah (01:07:37):

I would suggest Polygon, Salon, or MoonPay. I know it's three, but I wanted to give some breath in the Web3 space that might be exciting to people.

Lenny (01:07:45):

Great, great choices. What's a favorite TV show or movie that you've recently watched?

Jason Shah (01:07:48):

The Ken Burns Vietnam War series. I'm really into documentaries and history, and it's a really kind of compelling version of history that I've never seen before.

Lenny (01:07:58):

Awesome. Love that. Okay. Favorite interview question that you like to ask.

Jason Shah (01:08:02):

What is a risk you regret not taking, why, and what did you learn about yourself?

Lenny (01:08:08):

What do you look for in an answer there?

Jason Shah (01:08:10):

I think the biggest thing I look for is a growth mindset, to be able to reflect on an experience like that and be vocally self-critical without unproductively being hard on one's self, and I think that the dimension of asking about risk gets at their psychology and how do they think about not only their career, but if they were to work with me, how would they approach problem solving and taking bets on the business.

Lenny (01:08:33):

Awesome. Okay, final question. What's your least favorite vegetable?

Jason Shah (01:08:36):

Broccoli. I just removed some from a pizza last night that I really didn't want to eat.

Lenny (01:08:41):

Wow. Oh wow, okay. Even like steamed, cook, all the things?

Jason Shah (01:08:45):

There are no circumstances under which I'm excited about broccoli.

Lenny (01:08:49):

Oh man, you got to eat those veggies.

Jason Shah (01:08:51):

I know. I'm working on it.

Lenny (01:08:52):

Okay, Jason, this was amazing. Lived up to what I was hoping our second episode would be. Definitely better than our first which we'll leave on the cutting room floor. Two last questions. Where can people find you online? I assume Alchemy's hiring, so maybe pointing people there. And then how can listeners be useful to you?

Jason Shah (01:09:08):

Yeah, definitely. So, if you're interested in Alchemy and Web3, go to and click through to our jobs page from there. I'm online @0xShah. That is my crypto pseudonymous handle and happy to engage with folks there. And in terms of being helpful to me, I would love any feedback on anything that came up. I would love any products that people are working on. I also invest, and we also partner with a lot of products and teams at Alchemy, and I would love to meet anybody that's listening on the podcast too because I know Lenny's all about community and has kind of given so much back over the years that I would love to meet folks that are out there and get a chance to spend time talking about the products that you're all building.

Lenny (01:09:46):

Awesome. Thanks, Jason.

Jason Shah (01:09:48):

Thanks, Lenny.

Lenny (01:09:50):

Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at See you in the next episode.